86994-11-8

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 59839-58-6 hex-3-yne-1,6-diyl-bis(4-methylbenzene sulfonate) 
• 98194-56-0 tert-butyl-chlorosilane 
• 2117-12-6 4-(trimethylsilyl)but-3-yn-1-ol 

Downstream Products

• 1382991-38-9 N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide 
• 1382991-37-8 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide 
• 183208-72-2 N-[4-(1,1,1-trimethylsilyl)-3-butyn-1-yl]acetamide 

Relevant academic research and scientific papers

Enantioselective total synthesis of (+)- and (-)-nigellamine A2

The nigellamine alkaloids are dolabellane diterpenes displaying potent lipid metabolism-promoting activity. Total synthesis of (+)- and (-)-nigellamine A2 has been accomplished. Absolute stereochemistry of synthetic nigellamine A2 was established through an intramolecular asymmetric allylic alkylation using a Pd(phosphinooxazoline) catalyst. Other notable transformations include a radical alkynylation, a diastereoselective Nozaki-Hiyama-Kishi cyclization, and a regio- and stereoselective catalytic epoxidation. On the basis of X-ray crystallographic analysis of an optically active intermediate, we have confirmed the assigned absolute stereochemistry of the natural product. Minor modifications of the synthetic sequence outlined here should provide access to the other nigellamine alkaloids. Copyright

Synthesis of iboga alkaloids by Pd-catalyzed heteroannulation of 2-iodoaniline with an internal alkyne as the key step

A convenient synthetic route to the iboga-scaffolds is described. Important steps include a Pd-catalyzed regiospecific indole formation between internal alkyne-substituted isoquinuclidine and 2-iodoaniline. The final cyclization was done using Trost's Pd(II)-Ag(I) mixed-metal-mediated cyclization method originally developed for the synthesis of ibogamine. Both exo- (iboga) and endo-isomers (epi-iboga) at C-19 substitution with -CO2Me have been reported.

A bifunctional amino acid to study protein-protein interactions

Protein-protein interactions (PPIs) play crucial roles in regulating essentially all cellular processes. Photo-cross-linking represents a powerful method to study PPIs. To fulfil the requirements for the exploration of different PPIs, there is a continuous demand on the development of novel photo-reactive amino acids with diverse structural properties and functionalities. Reported herein is the development of a bifunctional amino acid termed dzANA, which contains a diazirine, for photo-cross-linking, and a terminal alkyne group, for bioorthogonal tagging. Using known PPIs between histone posttranslational modifications (PTMs) and their binding partners as models, we demonstrate that the dzANA-harbouring peptide-based photoaffinity probes could efficiently and selectively capture the weak and transient PPIs mediated by histone modifications. Our study indicates the potential of dzANA to identify and characterize unknown PPIs. This journal is

Total Synthesis of Kalimantacin A

The kalimantacins make up a family of hybrid polyketide-nonribosomal peptide-derived natural products that display potent and selective antibiotic activity against multidrug resistant strains of Staphylococcus aureus. Herein, we report the first total synthesis of kalimantacin A, in which three fragments are prepared and then united via Sonogashira and amide couplings. The enantioselective synthetic approach is convergent, unlocking routes to further kalimantacins and analogues for structure-activity relationship studies and clinical evaluation.

Construction of sequence-defined polytriazoles by IrAAC and CuAAC reactions

Here we report the first synthesis of sequence-defined polytriazoles, in which different side groups are sequentially anchored to the C-5 position of 1,2,3-triazole rings. By using efficient synthetic strategies based on IrAAC and CuAAC, different monodis

Synthetic method of natural product (-)-Psychotriasine

The invention relates to a synthetic method of a natural product (-)-Psychotriasine. The method comprises the following steps of: using a compound of a known formula 1 as an initial raw material, carrying out a series of reactions such as triphenylmethyl

Total synthesis of (±)-20: S -hydroxy-1,2-dehydro-pseudoaspidospermidine via a C-H activation/transannular cyclization strategy

A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.

Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis

The combination of triazole/gold (TA-Au) and Cu(OTf)2is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C?B bond formation.

Cross-Metathesis of Terminal Alkynes

Terminal acetylenes are amongst the most problematic substrates for alkyne metathesis because they tend to undergo rapid polymerization on contact with a metal alkylidyne. The molybdenum complex 3 endowed with triphenylsilanolate ligands, however, is capable of inducing surprisingly effective cross-metathesis reactions of terminal alkyl acetylenes with propynyl(trimethyl)silane to give products of type R1-C≡CSiMe. This unconventional way of introducing a silyl substituent onto an alkyne terminus complements the conventional tactics of deprotonation/silylation and excels as an orthogonal way of alkyne protecting group chemistry for substrates bearing base-sensitive functionalities. Moreover, it is shown that even terminal aryl acetylenes can be cross-metathesized with internal alkyne partners. These unprecedented transformations are compatible with various functional groups. The need to suppress acetylene formation, which seems to be a particularly effective catalyst poison, is also discussed.

Agri-Horticultural Pest Control Compositions Comprising 4-(3-Butynyl)Aminopyrimidine Derivatives

Agri-horticultural pest control compositions having outstanding control effect on pests, in particular, agri-horticultural pests, which comprise as active ingredients one or more 4-(3-butynyl)aminopyrimidine derivatives represented by the general formula [I], namely, where R1 is typically selected from among: a) phenyl c) —SiR5R6R7 (R5, R6, and R7 which may be the same or different represent a linear or branched alkyl having 1-6 carbon atoms, a linear or branched haloalkyl having 1-3 carbon atoms which is substituted by one halogen atom, a linear or branched cyanoalkyl having 1-3 carbon atoms which is substituted by one cyano group, and phenyl); d) hydropgen atom; R2 typically represents a hydrogen atom; R3 typically represents a hydrogen atom; R4 represents a hydrogen atom and one or more agri-horticultural pest control compounds selected from among agri-horticultural antimicrobial compounds, say, multi-site contact active compouns, nucleic acids synthesis inhibitory active compounds, mitosis and cell divesion inhibitory active compounds, and/or agri-horticultural insecticidal, miticidal or nematicidal compounds, say, acetylcholinesterase inhibitors, GABA-gated chloride antagonists, and sodium channel modulators. Since the 4-(3-butynyl)aminopyrimidine derivatives and the existing antimicrobial active compounds and/or insecticidal active compounds are used in admixture, the 4-(3-butynyl)aminopyrimidine derivatives which are useful as pest control agents, particularly as agri-horticultural pest control agents, need be used in smaller amounts and yet their antimicrobial or insecticidal activity can be improved.